Electrostatic effects on the reactions of cyclohexanone oxocarbenium ions
Electrostatic effects on the reactions of cyclohexanone oxocarbenium ions
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DOI：
10.1021/jo060968z
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发表时间：
2006-09-01
影响因子：
3.6
通讯作者：
Woerpel, K. A.
中科院分区：
文献类型：
--
作者：
Baghdasarian, Glen;Woerpel, K. A.
Nucleophilic substitution reactions of 4-substituted cyclohexanone acetals display different selectivities depending upon the electronic nature of the substituent. Alkyl groups favor equatorial positions in the oxocarbenium ions, but alkoxy groups prefer axial conformers. The reactions of acetals with alkoxy groups constrained to either equatorial or axial positions suggest that the presence of an axial alkoxy group distorts the oxocarbenium ion, changing its inherent preferences for facial attack.
